Showing Compound alpha-Tocopherol (FDB000565)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:37 UTC

Update date

2019-11-26 02:55:00 UTC

Primary ID

FDB000565

Secondary Accession Numbers

FDB005752

Chemical Information

FooDB Name

alpha-Tocopherol

Description

Constituent of many vegetable oils such as soya and sunflower oils. Dietary supplement and nutrient. Nutriceutical with anticancer and antioxidant props. Added to fats and oils to prevent rancidity. The naturally-occurring tocopherol is a single stereoisomer; synthetic forms are a mixture of all eight possible isomers Alpha-tocopherol is traditionally recognized as the most active form of vitamin E in humans, and is a powerful biological antioxidant. alpha-Tocopherol is found in many foods, some of which are custard apple, nopal, bitter gourd, and kumquat.

CAS Number

59-02-9

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(+)-alpha-Tocopherol	ChEBI
(2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol	ChEBI
(2R,4'r,8'r)-alpha-Tocopherol	ChEBI
(all-R)-alpha-Tocopherol	ChEBI
5,7,8-Trimethyltocol	ChEBI
D-alpha-Tocopherol	ChEBI
RRR-alpha-Tocopherol	ChEBI
Vitamin e	ChEBI
(+)-a-Tocopherol	Generator
(+)-Α-tocopherol	Generator
(2R,4'r,8'r)-a-Tocopherol	Generator
(2R,4'r,8'r)-Α-tocopherol	Generator
(all-R)-a-Tocopherol	Generator
(all-R)-Α-tocopherol	Generator
D-a-Tocopherol	Generator
D-Α-tocopherol	Generator
RRR-a-Tocopherol	Generator
RRR-Α-tocopherol	Generator
a-Tocopherol	Generator
Α-tocopherol	Generator
(R,R,R)-alpha-Tocopherol	ChEBI
(R,R,R)-a-Tocopherol	Generator
(R,R,R)-α-Tocopherol	Generator
(2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol	HMDB
a-D-Tocopherol	HMDB
alpha-delta-Tocopherol	HMDB
delta-alpha-Tocopherol	HMDB
Denamone	HMDB
Eprolin	HMDB
Phytogermin	HMDB
Phytogermine	HMDB
RRR-alpha-Tocopheryl	HMDB
Vitamin ea	HMDB
alpha-Tocopherol	ChEBI
(+)-2R,4'R,8'R-alpha-Tocopherol	HMDB
(+)-2R,4'R,8'R-α-Tocopherol	HMDB
(+)-2R,4’R,8’R-α-Tocopherol	HMDB
(2R,4’R,8’R)-α-Tocopherol	HMDB
3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-(2R)-2H-1-benzopyran-6-ol	HMDB
alpha-D-Tocopherol	HMDB
alpha-Vitamin E	HMDB
α-D-Tocopherol	HMDB
α-Vitamin E	HMDB
Almefrol	PhytoBank
Emipherol	PhytoBank
Etamican	PhytoBank
Evitaminum	PhytoBank
Profecundin	PhytoBank
Vitamin Ealpha	PhytoBank
Vitamin Eα	PhytoBank
(+)-a-tocopherol	biospider
(+)-alpha-tocopherol	biospider
(+)-α-tocopherol	Generator
(2R,4'R,8'R)-a-Tocopherol	biospider
(2R,4'R,8'R)-alpha-Tocopherol	biospider
(2R,4'R,8'r)-α-tocopherol	Generator
(2R)-3,4-dihydro-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol	HMDB
(all-r)-a-tocopherol	biospider
(r,r,r)-a-tocopherol	biospider
(r,r,r)-alpha-tocopherol	biospider
(R,R,R)-α-tocopherol	Generator
3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol, 9CI	db_source
a-tocopherol	biospider
Alpha-delta-tocopherol	biospider
Alpha-tocopherol	biospider
Antisterility vitamin	db_source
Covitol	biospider
D-alpha-tocopherol	biospider
D-α-tocopherol	Generator
Delta-alpha-tocopherol	biospider
E307	db_source
Ephanyl	biospider
Ephynal	db_source
Natopherol	biospider
RRR-alpha-tocopherol	biospider
RRR-alpha-tocopheryl	HMDB
Syntopherol	db_source
Tocopherol	biospider
Vitamin E?	db_source
α-tocopherol	Generator

Predicted Properties

Property	Value	Source
Water Solubility	7.0e-06 g/L	ALOGPS
logP	8.84	ALOGPS
logP	10.51	ChemAxon
logS	-7.8	ALOGPS
pKa (Strongest Acidic)	10.8	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	135.37 m³·mol⁻¹	ChemAxon
Polarizability	55.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C29H50O2

IUPAC name

(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol

InChI Identifier

InChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1

InChI Key

GVJHHUAWPYXKBD-IEOSBIPESA-N

Isomeric SMILES

CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C

Average Molecular Weight

430.7061

Monoisotopic Molecular Weight

430.381080844

Classification

Description

Belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Tocopherols

Alternative Parents

Substituents

Tocopherol
Diterpenoid
1-benzopyran
Benzopyran
Chromane
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alpha-tocopherol (CHEBI:18145 )
vitamin E (C02477 )
Fat-soluble vitamins (C02477 )
Vitamin E (LMPR02020000 )

Ontology

Thyroid cancer

Food

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Hormone

Modulator:

Immunomodulator

Industrial application:

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 80.87%; H 11.70%; O 7.43%	DFC
Melting Point	Mp 2.5-3.5°	DFC
Boiling Point	Bp0.03 140°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]25D +0.65 (EtOH)	DFC
Spectroscopic UV Data	[neutral] lmax 292 () (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0159-2900500000-03e8a824731610752eb3	2014-09-20	View Spectrum
GC-MS	alpha-Tocopherol, 1 TMS, GC-MS Spectrum	splash10-000i-1390000000-fc8c4f9b9405598ede7f	Spectrum
GC-MS	alpha-Tocopherol, 1 TMS, GC-MS Spectrum	splash10-00dr-9150010000-c4abc0e689e9b2476b9d	Spectrum
GC-MS	alpha-Tocopherol, 1 TMS, GC-MS Spectrum	splash10-0f79-1190040000-663296a69129a59be1a6	Spectrum
GC-MS	alpha-Tocopherol, non-derivatized, GC-MS Spectrum	splash10-000i-1390000000-fc8c4f9b9405598ede7f	Spectrum
GC-MS	alpha-Tocopherol, non-derivatized, GC-MS Spectrum	splash10-00dr-9150010000-c4abc0e689e9b2476b9d	Spectrum
GC-MS	alpha-Tocopherol, non-derivatized, GC-MS Spectrum	splash10-0f79-1190040000-663296a69129a59be1a6	Spectrum
Predicted GC-MS	alpha-Tocopherol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0aor-9886300000-b3225facac6ebdd8ddbd	Spectrum
Predicted GC-MS	alpha-Tocopherol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000l-7735900000-1585eb83c1211ebe95f2	Spectrum
Predicted GC-MS	alpha-Tocopherol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	alpha-Tocopherol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-9600100000-aaf885290800a10d3fb2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-01wr-9300000000-f0c814976a58a9d837ca	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0f79-1494700000-6b5f8f817c5a5429ed70	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positive	splash10-00lr-4910600000-1eda05dacf9642d7cea0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-a5860634bfd1ceb6833f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0159-0900500000-5a3bc17152cb61859b2c	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0842900000-f51286676592fd184193	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-1920000000-1994f86bec2bb4a77b9c	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-3930000000-02190bf16d5d85d44bce	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0110900000-c3541294fc60a7a8cc7e	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-0730900000-553c4898757f6876036c	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03e9-0920200000-276273a531fed5b3a2b0	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-3013900000-4985082235edff7c4b8c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05r1-9313200000-cbc230d5dd20c629ffab	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9320000000-5958d2e1d5b687b012c1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-d3ddef81c134412455e1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0310900000-30597e14cf876e4e4764	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-08g0-2982400000-371737325df4dbb523b2	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB00163

HMDB ID

HMDB01893

CRC / DFC (Dictionary of Food Compounds) ID

BDR14-R:BDR14-R

EAFUS ID

Not Available

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Alpha-Tocopherol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti-Alzheimeran	52217	An agent that inhibits the progression of Alzheimer's disease, reducing beta-amyloid plaque formation and neuroinflammation. Therapeutically, it improves cognitive function and memory, commonly used in managing mild to moderate Alzheimer's disease and other neurodegenerative disorders.	DUKE
Anti anginal	52217	An agent that reduces angina symptoms by improving blood flow to the heart, commonly used in managing angina pectoris, coronary artery disease, and other cardiovascular conditions, to alleviate chest pain and prevent cardiac complications.	DUKE
Anti-arthritic	52217	An agent that reduces joint inflammation and alleviates symptoms of arthritis, commonly used in managing rheumatoid arthritis, osteoarthritis, and other inflammatory joint disorders, to improve mobility and quality of life.	DUKE
Anti-asthmatic	49167	An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health.	DUKE
Anti-atherosclerotic	38070	An agent that prevents or slows the formation of atherosclerosis, a condition characterized by plaque buildup in arteries. It reduces inflammation, improves lipid profiles, and inhibits platelet aggregation, commonly used to manage cardiovascular diseases, such as coronary artery disease, and prevent heart attacks and strokes.	DUKE
Anti-cancer	35610	An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.	DUKE
Anti-cataract	52217	An agent that prevents or slows the formation of cataracts, reducing oxidative stress and inflammation in the lens of the eye, commonly used to manage age-related cataracts and other ocular disorders.	DUKE
Anti convulsant	52217	An agent that reduces or prevents seizures, commonly used in managing epilepsy, neuropathic pain, and mood disorders, by stabilizing abnormal electrical activity in the brain.	DUKE
Anti-dementia	52217	An agent that slows or prevents cognitive decline, reducing symptoms of dementia. It plays a biological role in neuroprotection, enhancing neuronal function and survival. Therapeutically, it is used to manage Alzheimer's disease, vascular dementia, and other neurodegenerative disorders, improving memory, cognition, and daily functioning.	DUKE
Anti-diabetic	52217	An agent that regulates blood sugar levels, enhancing insulin sensitivity or secretion. Therapeutically, it's used to manage diabetes, reducing symptoms and complications, and commonly prescribed to treat type 1 and 2 diabetes, as well as gestational diabetes.	DUKE
Anti-infarctal	52217	An agent that reduces myocardial infarct size, protecting against cardiac damage. It plays a biological role in inhibiting apoptosis and inflammation, promoting therapeutic applications in cardiovascular disease management, and is used to treat conditions such as myocardial infarction, heart failure, and cardiac arrhythmias.	DUKE
Anti-infertility	52217	An agent that enhances reproductive health, promoting fertility and conception. Its biological role involves regulating hormonal balance and improving reproductive function. Therapeutically, it is used to treat infertility disorders, with key medical applications in assisted reproduction, polycystic ovary syndrome (PCOS), and unexplained infertility.	DUKE
Anti-ischemic	52217	An agent that reduces or prevents tissue damage from inadequate blood flow, commonly used to manage angina, heart attacks, and strokes by improving oxygen delivery and reducing cardiac workload.	DUKE
Anti-maculitic		An agent that reduces macular inflammation, commonly used in managing age-related macular degeneration and diabetic macular edema, promoting vision preservation and reducing disease progression.	DUKE
Anti-mutagenic		An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.	DUKE
Anti neuropathic		An agent that relieves symptoms such as pain, numbness, and tingling caused by damage or disease affecting the somatosensory nervous system, commonly used in managing conditions like diabetes, shingles, and nerve injuries.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti-Parkinsonian	48407	An agent that alleviates symptoms of Parkinson's disease, enhancing dopamine levels and improving motor function, commonly used to manage tremors, rigidity, and bradykinesia in neurodegenerative disorders.	DUKE
Anti radicular		An agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.	DUKE
Anti-retinotic		An agent that inhibits retinoic acid activity, acting as a receptor antagonist. It plays a biological role in regulating cell growth and differentiation. Therapeutically, it has applications in managing retinoic acid-related disorders, with key medical uses including treatment of retinoic acid toxicity and certain types of cancer.	DUKE
Anti-rheumatic	52217	An agent that reduces inflammation and alleviates symptoms of rheumatic diseases, such as arthritis. It plays a biological role in modulating the immune system and inhibiting pro-inflammatory pathways. Therapeutically, anti-rheumatics are used to manage conditions like rheumatoid arthritis, lupus, and osteoarthritis, reducing pain, swelling, and joint damage. Key medical uses include slowing disease progression and improving quality of life for patients with chronic rheumatic conditions.	DUKE
Anti-stroke	52217	An agent that prevents or reduces the severity of stroke, typically by inhibiting blood clot formation or improving cerebral blood flow, commonly used in managing cardiovascular diseases, preventing stroke recurrence, and reducing stroke-related brain damage.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Antitumor promoter	35610	An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Cardioprotective	38070	An agent that protects the heart from damage, reducing the risk of cardiovascular disease. It plays a biological role in mitigating cardiac stress and injury, with therapeutic applications in preventing heart attacks, strokes, and arrhythmias, and key medical uses in treating hypertension, heart failure, and coronary artery disease.	DUKE
Circulotonic		A cardiac stimulant that enhances cardiovascular function, increasing cardiac output and blood pressure. Therapeutically, it's used to treat hypotension, shock, and heart failure, improving circulation and overall cardiovascular health. Key medical uses include managing cardiogenic shock, post-operative hypotension, and severe dehydration.	DUKE
Immunomodulator	50846	An agent that regulates the immune system, modifying its response to maintain balance. Therapeutically, it's used to treat autoimmune diseases, prevent transplant rejection, and manage chronic inflammatory conditions, such as rheumatoid arthritis and multiple sclerosis.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Nuclear receptor subfamily 1 group I member 2	NR1I2	O75469
Glutamate--cysteine ligase catalytic subunit	GCLC	P48506
Glutathione S-transferase Mu 3	GSTM3	P21266
Glutathione S-transferase omega-1	GSTO1	P78417
Glutathione S-transferase A2	GSTA2	P09210
Glutathione S-transferase P	GSTP1	P09211
Serine palmitoyltransferase 1	SPTLC1	O15269
Alpha-tocopherol transfer protein	TTPA	P49638